International Journal of ChemTech Research

CODEN( USA): IJCRGG ISSN : 0974-4290

Vol. 3, No.4, pp 1891-1896, Oct-Dec 2011

Application of Schiff bases and their metal

complexes-A Review
Anant Prakash*, Devjani Adhikari
1
Department of Chemistry, Khandelwal College of Management Sciences and
Technology, Bareilly, India
2
Inorganic and Bioinorganic Research Lab, Department of Chemistry, Govt.
Postgraduate College, Ranikhet- 263645 (Uttarakhand), India.

*Corres.author: apgangwar_bly@rediffmail.com
Phone 91 9412066814

Abstract: Schiff bases are versatile ligands which are synthesized from the condensation of an amino compound
with carbonyl compounds. These compounds and their metal complexes are very important as catalysts in various
biological systems, polymers, dyes and medicinal and pharmaceutical fields. Their use in birth control, food
packages and as an O2 detector is also outlined. This review summarizes the applications of Schiff bases and their
complexes.
Keywords: Schiff bases, metal complexes, biological activity, nonlinear optical properties.

Introduction successful models of biological compounds [5]. Not

only have they played a seminal role in the
Schiff bases derived from an amino and carbonyl development of modern coordination chemistry, but
compound are an important class of ligands that also they can also be found at key points in the
coordinate to metal ions via azomethine nitrogen and development of inorganic biochemistry, catalysis and
have been studied extensively [1]. In azomethine optical materials [6].
derivatives, the C=N linkage is essential for biological
activity, several azomethines were reported to possess
(1) Antimicrobial Activities
remarkable antibacterial, antifungal, anticancer and
diuretic activities [2]. Schiff bases have wide Antibacterial Activities
applications in food industry, dye industry, analytical Schiff base derived from indoline-2, 3-dione and 2-
chemistry, catalysis, fungicidal, agrochemical and aminobenzoic acid and its Tin complex showed
biological activities[3].With the increasing incidence antibacterial activity against Staphylococcus aureus.
of deep mycosis, there has been increasing emphasis The results compared with standard drug (Imipinem)
on the screening of new and more effective have indicated that compounds were active but activity
antimicrobial drugs with low toxicity. Schiff-base was lesser than the standard drug. This activity might
complexes are considered to be among the most be due to the presence of a hydroxyl and phenyl group
important stereochemical models in main group and [7]. The increased activity in the organotin complexes
transition metal coordination chemistry due to their may be due to the coordination and polarity of a
preparative accessibility and structural variety[4].A tin(IV) atom with oxygen of the ligand. The order of
considerable number of Schiff-base complexes have increasing activities is ligand < MeSnL < PhSnL <
potential biological interest, being used as more or less BZ3SnL, the results matched with the previously
Anant Prakash et al /Int.J. ChemTech Res.2011,3(4) 1892

reported data for the biological activity of organotin 2,6-pyridinecarboxaldehydebis(p-

complexes [8]. Complexes of hydroxyphenylamine(L1), 2,6-pyridinecarbox -
2
Co(II),Cu(II),Ni(II),Mn(II) and Cr(III) with Schiff aldehydebis(o-hydroxyphenylamine(L ) showed anti -
bases derived from 2,6-diacetylpyridine and 2-pyridine bacterial activities. The data obtained reflect that the
carboxaldehyde with 4-amino-2,3-dimethyl-1-phenyl- two Schiff base ligands L1 and L2 have moderate
3-pyrozolin-5-one show antibacterial and antifungal activity in comparison with Staphylococcus aureus,
activities against Escherichia coli, Staphylococcus Escherichia coli and less active in comparison with
aureus, Klebsiella pneumoniae, Mycobacterium Pseudomonas aeruginosa. L1 ligand shows a moderate
Smegmatis, Pseudomonas aeruginosa, Enterococcus activity towards Bacillus subtilis while L2 ligand is less
cloacae, Bacillus megaterium and Micrococcus leteus. active. The remarkable activity of the two Schiff base
The results showed that L1 ligand has a greater effect ligands may be arise from the pyridyl-N and the
against E. coli than the other bacteria while it has no hydroxyl groups which may play an important role in
activity against S. aureus. Metal complexes have a the antibacterial activity[13] as well as the presence of
greater effect than L2 against almost all bacteria [9]. two imine groups which imports in elucidating the
The Schiff base 4-chloro-2-(2-morphiolinoethylimino) mechanism of transformation reaction in biological
methylphenolato methanolchloro and its Zn(II) system[13]. Tetra and hexacoordinate metal chelate
complex were screened for antibacterial activity complexes of phosphate Schiff base ligands were
against two Gram positive bacterial strains (B. subtilis found to be possess remarkable bacterial properties, it
and S. aureus) and two Gram-negative bacterial is however interesting that the biological activity gets
strains(E. coli and P. fluorescence) by the MTT enhanced on undergoing complexation with the metal
method. The Schiff base showed significant activity ions[14]. Neutral tetradentate complexes of transition
against two Gram-negative bacterial strains with MIC metals with Schiff bases derived from 2-
of 12.5gmL-1but was inactive against two Gram aminophenol/2-aminothiophenol and 1-phenyl-2,3-
negative bacterial strains. The Zn complex showed a dimethyl-4(4-iminopentan-2-one)-pyrazol-5-one
wide range of bactericidal activities against the Gram showed antimicrobial activity against Staphylococcus
positive and Gram negative bacteria, were potent than, aureus, Bacillus subtilis, Klebsiella imeumoniae,
or similar with commercial antibiotics (Kanamycin Salmonella typhi, Pseudomonous aeruginosa, Shigella
and penicillin) [10]. Bidentate complexes of Co(II), flexneri, Aspergillus niger and Trichoderma viridi.
Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) with Most of the complexes have higher activity than the
benzofuran-2-carbohydrazide and benzaldehyde free ligand[15]. Complexes of transition metal with
[BPMC] or 3,4-dimethoxybenzalde hyde[BDMePMC] Schiff base derived from 2,3-
showed biological activities. Co(II) and Cd(II) dihrdrazinoquinoxaline(DHQ) showed antimicrobial
complexes of [BPMC] are moderately active toward acyivity. Preliminary testing of the ligand and metal
E.coli whereas Cu(II), Zn(II) and Ni(II) complexes of complexes for antimicrobial activity on the gram
[BPMC] and Cu(II) and Zn(II) complexes of positive S.aureus and gram negative E.coli shows that
[BDMeOPMC] are more active against S.aurious as the ligand is active only against S.aureus and the
compared to free ligands. None of the complexes are activity is enhanced by complexation. The metal
active against A.niger, but in the case of A.fumigatus, complexes exhibit more bacreriostatic activity against
Cu(II),Co(II), Ni(II) and Cd(II) complexes of E.coli. The appearance of activity may be due to
[BDMeOPMC] are more active than the parent synergistic mechanism[16]. A tridentate Schiff base
ligands[11]. Amino acid Schiff base derived from 2- derived from the condensation of S-
hydroxy-5-methylacetophenone and glycine and its benzyldithiocarbazate with salicyldehyde and
transition metal complexes showed bacterial activities. transition metal complexes showed significant
The ligand was bacteriostatic against bacterial strains bioactivity against Pseudomonas aeruginosa (gram
except Proteus vulgaris, Shigella flexneri, and Bacillus negative) and Bacillus cereus (gram positive) while the
coagulans. All complexes are either resistant or less uranium analogue was effective against Bacillus
sensitive against P.vulgaris. However compared to the cereus and showed very weak activity against Candida
antibacterial activity of the standard antibiotic albicans fungi[17].
streptomycin, the activity exhibited by the ligand and
metal complexes was lower. The metal complexes Antifungal Activities
showed to exhibited higher activity than the free ligand
against the same organism under identical The microbial activity of the N-(2-hydroxy-1-
experimental conditions, such increased activity of the naphthalidene)phenylglycine and its transition metal
metal chelates can be explained on the basis of complexes was investigated. From the antifungal
chelation theory[12]. Mixed ligand complexes with screening data it is concluded that the activity of the
ligand has increased upon complexation. Cu(II), Ni(II)
Anant Prakash et al /Int.J. ChemTech Res.2011,3(4) 1893

and Co(II) complexes have shown better antifungal derived from the condensation of S-
activity compared to the ligand and the corresponding benzyldithiocarbazate with salicyldehyde and its Zn,
metal salts[18]. Two bidentate Schiff base ligands 2- Sb, Cu complexes showed cytotoxic properties[27].
(2-hydroxy-3, 5-dichloro/dibromo) benzaldehyde-[4- Copper(II) complexes containing Schiff bases derived
(3-methyl-3-mesitylcyclobutyl)-1, 3-thiazol-2- from S-benzyldthiocarbazate and saccharinate showed
yl]hydrazone, L 1H, L2H and their metal complexes anticancer properties. The complexes were highly
were tested against a yeast-like fungus C.albicans[19]. active against the leukemic cell line (HL-60) but only
The fungicidal effect of salicylaldimine containing [Cu(NNS)(sac)] was found to exhibit strong
formaldehyde and piperazine moity and its metal cytotoxicity against the ovarian cancer cell line (Caov-
polychelates were determind against two yeast 3). The activities being higher than the standard
Candida albicans, Aspergillus. The Cu(II)-polychelate anticancer drug Doxorubicin[28]. Compexes of
exhibited high activity against Candida albicans and chromium(III) are much less cytotoxic than
the other show mild activity. The presence of N and O chromium(VI) to cultured human cells[29].
donor groups in the ligand and its metal polychelates Chromium(III) is an essential nutrient that is involved
inhibited enzyme production because enzymes that in the glucose tolerance factor(GTF) in maintenance of
require free hydroxyl group for their activity appear to normal carbohydrate and lipid metabolism[30].
be especially susceptible to deactivation by the metal
ion of polychelates. All the metal polychelates are Antiviral Activities
more toxic than the ligand[20]. Neutral complexes of
Co(II), Ni(II), Cu(II) and Zn(II) with Schiff bases Schiff bases of gossypol show high antiviral
derived from 3-nitrobenzylidene-4- aminoanttipyrine activity[31]. Silver complexes in oxidation state I
and aniline(L1)/p-nitroaniline(L2)/p-methoxyaniline showed inhibition against Cucumber mosaic virus;
(L3) showed antifungal activity. A comparative study glycine salicylaldehyde Schiff base Ag(I), gave
of the MIC values for the ligands and their complexes effective results up to 74% towards C.mosaic
indicates that the complexes exhibit higher virus[32].
antimicrobial activity. Such increased activity of the
complexes can be explained on the basis of overtones Synthetic Action on Insecticides
concept and Tweedys chelation theory[21]. Inhibition Schiff base derived from sulfane thiadizole and
is enhanced with the introduction of an electron salicylaldehyde or thiophene-2-aldehydes and their
withdrawing nitro group in the phenyl ring[22]. complexes show toxicities against insects[33]. -
Semicarbazones and thiosemicarbazones complexes of Aminoacid acts as intermediate in synthesis of
Ni(II) metal showed antifungal activities against 11 photostable pyrthriod insecticides[34]. Flourination on
pathogenic fungi. The complexes were moderate active aldehyde part of Schiff base enhances insecto
against all pathogenic fungi and much lower than those acracicidal activity[35]. Schiff bases (thiadiazole
of standard fungicide Nistatin[23]. Co(II),Ni(II) and derivatives with salicylaldehyde or o-vanillin) and
Cu(II) complexes with Schiff base 3,3-thiodipropionic their metal complexes with Mo(II) show insecticidal
acid bis(4-amino-5-ethylimino-2,3-dimethyl-1-phenyl- activities against bollworm and promote cell survival
3-pyrazoline showed antifungal activity against rate of mung bean sprouts[36].
Alternaria brassicae, Aspergillus niger and Fusarium
oxysprum and results indicate that the complexes show Plant Growth Regulator
the enhanced activity in comparison to free ligand[24].
N-acetylated compounds show growth inhibitory
Antitumor and Cytotoxic Activities activity with seedling of wheat, rye and barley[37].
Schiff bases show remarkable activities on plant
Metal complexes of Schiff base derived from 2- hormone such as the auxins on root growth[38]. Schiff
thiophenecarboxaldehyde and 2-aminobenzoic acid base of ester and carboxylic acid show remarkable
(HL) have been recommended and/ or established a activity as plant growth hormone[39]. Schiff bases of
new line for search to new antitumor particularly when thiodiazole have good plant growth regulator activity
one knows that many workers studied the possible towards auxin and cytokine[40].
antitumor action of many synthetic and semi synthetic
compounds e.g. Hodnett et al. and Hickman[25]. Such Other Therapeutic Activities
compounds may have a possible antitumor effect since
Gram-negative bacteria are considered a quantitative Several Schiff bases possess anti inflammatory,
microbiological method testing beneficial and allergic inhibitors reducing activity radical scavenging,
important drugs in both clinical and experimental analgesic and anti-oxidative action[41]. Thiazole
tumor chemotherapy[26]. A tridentate Schiff base derived Schiff bases[42] show analgesic and anti-
Anant Prakash et al /Int.J. ChemTech Res.2011,3(4) 1894

inflammatory activity. Schiff base of chitosan and (OH2)2]ClO4 was reported[53]. Ternary complexes of
carboxymethyl-chitosan shows an antioxidant activity Cu(II) containing NSO donor Schiff base showed
such as superoxide and hydroxyl scavenging. Furan DNA cleavage activity. In the presence of 3-
semicarbzone metal complexes exhibit significant mercaptopropionic acid (5mM) as a reducing agent,
anthelmintic and analgesic activites[42]. the complexes (40 M) show efficient DNA cleavage
activity giving the order NSO-dppz > ONO-dppz >
(2) Catalysts NSO-dpq > ONO dpq[54].
Co(II), Fe(III) and Ru(III) complexes of Schiff bases
(4) Dyes
derived from hydroxy benzaldehyde are used in
oxidation of cyclohexane into cyclohexanol and Chromium azomethine complexes, cobalt complex
cyclohexanone in presence of hydrogen peroxide. The Schiff base[55], unsymmetrical complex 1:2
most efficient catalysts are the Fe(III) complexes chromium[56] dyes give fast colours to leathers, food
which is unusual because, in general, the cobalt(II) packages, wools etc. Azo groups containing metal
complexes have high activity for alkane oxidation complexes[57] are used for dying cellulose polyester
reactions[43]. Chromium-salen complexes are well- textiles. Some metal complexes are used to mass dye
known catalysts both in heterogeneous and polyfibers[58]. Cobalt complex[59] of a Schiff base
homogeneous[44]. Binucleating complexes of Fe, Co, (salicylaldehyde with diamine) has excellent light
Ni, Zn with Schiff bases resistance and storage ability and does not degrade
neytralbis(iminopyridyl)benzene and monoanionic even in acidic gases (CO2). Novel tetradentate Schiff
bis(iminopyridyl)phenolate acts as catalysts in the base acts as a chromogenic reagent for determination
oligomerisation of ethylene[45]. New manganese(II) of Ni in some natural food samples[60].
and manganese(III) complexes of substituted N,N-
bis(salicylidine)-1,2-diimino-2-methylene appear to be (5) Polymer
efficient models for peroxidase activity[46]. New
Copper(II) complexes of indoxyl thiosemicarbazone Photochemical degradation of natural rubber yield
(ITSC) show one pair of well defined reduction peaks amine terminated liquid natural rubber(ATNR) when
at different potential in the forward scan, which carried out in solution, in presence of
represent the reduction of Cu++ to Cu+ by one electron ethylenediamine[60]. ATNR on reaction with glyoxal
process and subsequent oxidation of Cu+. The quasi- yield poly Schiff base[60], which improves aging
reversible nature of the Cu++/Cu+ is due to inherent resistance. Organocobalt complexes with tridentate
reducing tendency of thiosemicarbazone ligands[47]. Schiff base act as initiator of emulsion polymerization
Ruthenium and cobalt complexes with Schiff bases and co-polymerization of dienyl and vinyl
bis-salicylaldehyde-o-phenylene-diaimine(saloph) and monomers[61].
substituted(Cl,Br and NO2) oxidize -pinene into
camphene, 2,7,7-trimethyl ss pinene(3-oxatricyclo- (6) Miscellaneous Applications
4,1,1,o2,4-octane), 2,3-epoxy, campholene aldehyde Transition metal complexes with 1, 10-phenanthroline
and D-verbenone[48]. Ni(II) complexes with and 2, 2-bipyridine are used in petroleum refining[62].
bidentate(NN) ligands become an efficient catalyst Popova and Berova reported that copper is good for
precursor for olefin oligomerisation in presence of an liver function, its level in blood and urine has
activator[49]. A wide variety of cobalt(II) complexes influence in pregnancy disorders, nephritis hepatitis,
are known to bind dioxygen more or less reversibly leprosy, anemia and leukemia in children[63]. NLO
and are therefore frequently studied as model Metal complexes of Schiff base derived from
compounds for natural oxygen carrier and for their use tetradentate precursor 1-phenylbutane-1, 3-dionemono
in O2 storage, as well as in organic syntheses due to S-methylisothiosemicarbazone with o-hydroxy
their catalytic properties under mild conditions[50]. benzaldehyde or its phenylazoderivative showed
nonlinear optical (NLO) properties. A comparison
(3) Antifertility and Enzymatic Activity between complexes of different metals with the same
About 20 Zinc enzymes are known in which Zinc is phenylazo-substituted ligand indicated that the NLO
generally tetrahedrally four coordinate and bonded to response strongly depends upon the electronic
hard donor atoms such as nitrogen or oxygen[51]. The configuration of the metal center[64]. It has been
Schiff base complexes of 2-pyridinecarboxaldehyde reported that Zinc(II) complexes with Schiff bases type
and its derivatives have been reported to posses high chelating ligands can be used as an effective emitting
super oxide dismutase activities[52]. Recently, the layer[65]. In addition, it has also been shown that
interaction of DNA with complexes [Cr(Schiff base) Zinc(II) complexes with benzothiazoles, which are
Anant Prakash et al /Int.J. ChemTech Res.2011,3(4) 1895

oxidized forms of benzothiazolines are deficiency[68]. Amino acid Schiff base complexes
luminescent[66]. Zinc(II) and Cadmium(II) complexes derived from 2-hydroxy-1-naphthaldehydes are
with N2S2 -Schiff base ligands are a new class of important due to their use as radiotracers in nuclear
luminescent compounds, and the careful derivatization medicine[69]. Macrocyclic Schiff bases of
of the substituents on the pendent phenyl rings permits Dithiocarbazic acid have many fundamental biological
a finetuning of the emission wavelength[67]. Bakers functions, such as photosynthesis and transport of
yeast contains a benzofuran derivative which acts as an oxygen in mammalian and other respiratory
antioxidant preventing haemorrhagine liver necrosis in system[70].
rats and haemolysis of red cells in vitamin E

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